Chicago for a Guys Getaway

When we feel the weight of the world on our shoulders, we know it's time to get away and put some work-play balance back in our lives. And what better way than to put aside responsibilities than to make some memories with best buds in the Windy City? We've put together a guide to the best dining, drinking, shopping and adrenaline-inducing activities that are all for the boys.

Sarah Perkins

About the author

Even though she grew up in a small suburb north of Chicago, Sarah knew she was meant for somewhere bigger, more excit...

Feast away with your closest friends at this classy steakhouse on the Chicago River. All of the steak is certified USDA Prime Beef dry aged for 35 days and butchered onsite—with so many ways to customize your meat, you'll have a hard time finding a bad cut here. There's a reason so many celebrities flock here, including the Blackhawks.

Time to take on your bros on the racetrack—K1 Speed has all the indoor go-kart fun you could ever ask for. The Chicago area has two locations: Buffalo Grove and Addison, both complete with completely electric karts to have you zooming up to 45 mph. When you're not on the course, grab a beer at the bar and play a game of billiards.

If you're looking to hit the town with your boys, make sure you look good. Lincoln Park's The Tie Bar carries the accessories to give your outfit a pop when you're out for the night. Look for the Chicago themed collection, along with celebrity collaborations like Dwayne Wade's favorite prints. The store also carries select button downs.

Nothing says bro bonding like sipping whiskey. Good thing Untitled Supper Club has over 400 American varieties showcased in its whiskey library. Kick back in the lounge in a leather club chair for some good conversation, or grab a booth near the stage to take in a live performance. Thursday nights feature steamy Unbridled shows.

Want a memorable experience for the ages? Get yourself in a helicopter with CHE Tours to see Chicago in a whole new way. Your pilot is not only a flying expert, but a keeper of history and fun facts as you soar over the city. We guarantee there isn't a quicker way to get more likes on Instagram.

Shopping trips aren't just for the ladies—men need to stock up on the basics too. At UNTUCKit, you'll find an assortment of shirts that give you the sophistication of a button down without the awkward length of having to tuck it in. These toppers are the perfect transition from day to night—a big plus when traveling.

Head to this Logan Square brewery and brewpub to sip hops brewed up onsite. Complimentary guided tours are offered Wednesday-Sunday to view one of the largest breweries in the state. The brewpub is also a popular spot for weekend brunch—wash down country fried chicken pizza with one of the craft brews on tap.

For a relaxing day outside, head to the city's most recognizable green space: Millennium Park. Take essential photos with Cloud Gate and towering Crown Fountain, then choose a grassy spot under Pritzker Pavilion. Head to neighbor Maggie Daley Park for rock climbing and the ice skating ribbon turn skate park in the summer.

This museum is perfect for you history buffs. Learn about military history in this historic building in the Loop. The "Face of War" exhibit is especially compelling, focusing on the Vietnam War and artifacts from the Department of the Army Special Photographic Office. Rare book collections are also housed here.

No trip to Chicago is complete without deep dish pizza. And at Lou Malnati's, you're getting some of the best in the city. Challenge each other to an eating contest with these gigantic pies. Or kick back and catch a game on TV while sharing your favorite toppings. One thing is for sure—you won't walk away hungry.

Pampering isn't just for the ladies. This upscale spa and salon with several Chicago area locations offers services that use products and techniques just for men, including gentleman-specific facials, manicures and pedicures, a full back and chest wax treatment, and deep tissue massages perfect for pre- or post-workout.

It's game on at this two-story ping pong club and bar. Make sure to sign up ahead of time for a table for you and three buddies. When you're not dominating the paddles, browse the extensive food and cocktail menu while relaxing on chic lounges. We're fans of the crispy chicken and biscuits and the Salt Lick Susan drink.